5802-17-5

Basic information

• Product Name: 6-Methoxy-4-chromanone
• Synonyms: 6-Methoxy-4-chromanone;6-methoxychroman-4-one;4H-1-Benzopyran-4-one, 2,3-dihydro-6-Methoxy-;2,3-Dihydro-6-methoxy-4H-benzopyran-4-one;4-Chromanone, 6-methoxy-
• CAS NO: 5802-17-5
• Molecular Formula: C₁₀H₁₀O₃
• Molecular Weight: 178.1846
• Mol File: 5802-17-5.mol
• Article Data: 22

Chemical Properties

• Melting Point: 48 °C
• Boiling Point: 318.6°C at 760 mmHg
• Flash Point: 137.5°C
• Appearance: /
• Density: 1.205
• Vapor Pressure: 0.000358mmHg at 25°C
• Refractive Index: 1.546
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 6-Methoxy-4-chromanone(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Methoxy-4-chromanone(5802-17-5)
• EPA Substance Registry System: 6-Methoxy-4-chromanone(5802-17-5)

Safety Data

• Statements: 43
• Safety Statements: 36/37
• Hazardous Substances Data: 5802-17-5(Hazardous Substances Data)

Usage

General Description

6-Methoxy-4-chromanone is a chemical compound with the molecular formula C11H10O3. It is a member of the chromanone family, which are bicyclic organic molecules containing a benzofuranone ring system. 6-Methoxy-4-chromanone is characterized by the presence of a methoxy group at the 6-position of the chromanone ring, and has been found to exhibit various biological activities, including antioxidant and anti-inflammatory properties. It is also being studied for its potential therapeutic applications, particularly in the treatment of neurodegenerative diseases and cancer. 6-Methoxy-4-chromanone is commonly used as a building block in organic synthesis and medicinal chemistry research.

InChI:InChI=1/C10H10O3/c1-12-7-2-3-10-8(6-7)9(11)4-5-13-10/h2-3,6H,4-5H2,1H3

Upstream product

• 20811-60-3 3-(4-methoxyphenoxy)propanoic acid 
• 105630-28-2 (6-methoxy-2H-chromen-4-yl)methanol 
• 115997-63-2 1-((3-bromoprop-2-yn-1-yl)oxy)-4-methoxybenzene 
• 17061-86-8 1-methoxy-4-(2-propynyloxy)benzene 
• 6279-84-1 β-(m-methoxyphenoxy)propionitrile 
• 150-19-6 O-methylresorcine 
• 1181403-94-0 C₁₀H₁₁ClO₃ 
• 92971-94-3 β-(4-methoxyphenoxy)propionaldehyde ethylene acetal 
• 63815-39-4 2-(4-Methoxyphenoxy)cyanoethane 
• 105630-27-1 4-(4-methoxyphenoxy)but-2-yn-1-ol 
• 150-76-5 4-methoxy-phenol 
• 911831-33-9 5-methoxy-2-(2-tosyloxy-ethoxy)-benzaldehyde 
• 117543-22-3 1-(3-Chloro-prop-2-ynyloxy)-4-methoxy-benzene 
• 117543-34-7 4-chloro-6-methoxy-2H-chromene 

Downstream Products

• 132828-22-9 3-cinnamylidene-6-methoxychroman-4-one 
• 885604-53-5 (E)-3-[(4-hydroxyphenyl)methylene]-6-methoxy-chroman-4-one 
• 80096-64-6 6-hydroxy-2,3-dihydro-4H-chromen-4-one 
• 724788-41-4 3-Bromo-6-methoxy-4-quinolone 
• 116004-86-5 6-methoxychroman-4-one O-tosyl oxime 
• 1370470-34-0 4-(4-fluorophenyl)-6-methoxy-2H-chromene-3-carbaldehyde 
• 1370544-73-2 1-((4-(4-fluorophenyl)-6-methoxy-2H-chromen-3-yl)methyl)pyrrolidine 
• 1370470-33-9 4-(4-fluorophenyl)-6-methoxy-2H-chromene 
• 130688-90-3 3-[1-Benzo[1,3]dioxol-5-yl-meth-(E)-ylidene]-6-methoxy-chroman-4-one 
• 123671-92-1 (+)-(4aR,10bR)-3,4,4a,10b-tetrahydro-4-propyl-2H,5H-<1>benzopyrano<4,3-b>-1,4-oxazin-9-ol 

Relevant articles and documents

Design, synthesis and preliminary bioactivity evaluation of bitopic benzopyranomorpholine analogues as selective dopamine D3 receptor ligands as anti-drug addiction therapeutic agents

Three series of bitopic benzopyranomorpholine analogues were designed, synthesized, and evaluated as a novel class of selective ligands for the dopamine D3 receptor. Binding affinities of target compounds were determined using the method of radioligand binding assay. Most compounds demonstrated considerable binding affinities and selectivity for D3 receptor. Besides, the compounds were screened for their ability to alleviate withdrawal symptoms of opioid addiction in animal behavioral models. The results showed that compound 20h displayed nanomolar affinity for the D3R, and exhibited anti-drug addiction efficacy in the animal model of of naloxone-induced withdrawal symptoms in morphine-dependent mice.

Facile access to chiral 4-substituted chromanes through Rh-catalyzed asymmetric hydrogenation

Rh/ZhaoPhos-catalyzed asymmetric hydrogenation of a series of (E)-2-(chroman-4-ylidene)acetates was successfully developed to prepare various chiral 4-substituted chromanes with high yields and excellent enantioselectivities (up to 99percent yield, 98percent ee). Moreover, the gram-scale hydrogenation could be performed well in the presence of 0.02 molpercent catalyst loading (TON = 5000), the hydrogenation product was easily converted to access other important compounds, which demonstrated the synthetic utility of this asymmetric catalytic methodology.

Synthesis of Flavanones via Palladium(II)-Catalyzed One-Pot β-Arylation of Chromanones with Arylboronic Acids

A total of 47 flavanones were expediently synthesized via one-pot β-arylation of chromanones, a class of simple ketones possessing chemically unactivated β sites, with arylboronic acids via tandem palladium(II) catalysis. This reaction provides a novel route to various flavanones, including natural products such as naringenin trimethyl ether, in yields up to 92percent.